


The Jester's Gambit

by aunt_zelda



Category: Critical Role (Web Series)
Genre: Alternate Universe - Modern Setting, Alternate Universe - Spies & Secret Agents, Chess, Established Relationship, Exhibitionism, F/M, Flirting, Kissing, M/M, Multi, Polyamory, Pre-Relationship, Stakeout, Voyeurism
Language: English
Status: Completed
Published: 2020-12-31
Updated: 2020-12-31
Packaged: 2021-03-11 00:08:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,483
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28445904
Author URL: https://archiveofourown.org/users/aunt_zelda/pseuds/aunt_zelda
Summary: “I see what you’re doing over there. You’ve been at it ever since we left HQ.” Jester waves a hand. “Or, wait, no, before then. That mission in Singapore? You were totally flirting in that club.”“Jester we are not flirting.” Essek protests.“For a spy, you are a terrible liar, Essek.” Caleb smirks. “You should work on that.”
Relationships: Jester Lavorre/Caleb Widogast, Jester Lavorre/Essek Thelyss/Caleb Widogast
Comments: 5
Kudos: 54
Collections: Critmas Exchange 2020





	The Jester's Gambit

**Author's Note:**

  * For [flammablehat](https://archiveofourown.org/users/flammablehat/gifts).



> Wanted to write you a treat.

Caleb and Essek are playing chess, again. 

Jester is watching out the window. She hates stakeouts and this one is especially monotonous. She’s already sketched the street their room overlooks a dozen times and made studies of the light. She’s noted ideal locations for snipers and structural issues that could be exploited. She’s counted fifty-seven red cars, seventy-two blue cars, and two pink cars. 

“This is so boring!” Jester groans.

“We could practice your Russian again,” Essek suggests. “Your accent is too obvious. You should work on that.”

“Eugh, no! Why don’t you two do something entertaining?” Jester asks, glancing over her shoulder at the two men. 

“What do you suggest?” Caleb asks, still staring down at the board. 

“Oh, I don’t know. Finally quit flirting and start fucking?”

 _That_ makes Caleb look up from the chess board. 

“Excuse me?” Essek asks faintly. 

“I see what you’re doing over there. You’ve been at it ever since we left HQ.” Jester waves a hand. “Or, wait, no, before then. That mission in Singapore? You were totally flirting in that club.” 

“Jester we are not flirting.” Essek protests. 

“For a spy, you are a terrible liar, Essek.” Caleb smirks. “You should work on that.”

Essek stares at Caleb. “If this is some kind of joke being made at my expense, I do not appreciate it.” His voice is flat. 

“Joke? Essek, no.” Caleb’s voice goes soft. “My flirtation with you is not in jest.”

Jester squirms in her chair. “Essek, if you’re worried, Caleb looked at me the exact same way for months and months before I got him to say anything out loud. He’s not lying or joking.”

Essek stands up. “I need to –” he looks at the door to the hallway, remembering they aren’t permitted to leave unless their quarry has been sighted. “… damn.” 

Jester feels a rare emotion, mortification, creeping up her spine. She shivers and returns to her observation out the window. From the sounds of things, the chess game has been abandoned behind her. Caleb is back to reviewing transcripts and Essek is listening to recordings again. 

~*~

“They’re being so _stupid_.” Jester rolls her eyes, concluding her update to Artagan back at HQ. She’s in the bathroom with the shower going, obscuring her words to the men outside. 

“Then I’m afraid it’s up to you to be the catalyst, my dear. You’re ever so good at that.” Artagan chuckles. 

“You’re right, I am!” Jester smiles. “Well I already have Caleb, I guess I should work on Essek first?” 

“Or show Essek what he’s missing.” Artagan muses. “That man has been devoted to his job all his life. Show him what he could have, and that shell of his will start to crumble I have no doubt.”

“He’s not a turtle!” Jester protests. “Though, well, he kinda is.” She giggles at the idea of Essek curling up inside a turtle shell. Something to draw later. 

“I wish you luck, but you’ll hardly need that.” Artagan says. “I have every confidence in your abilities.” 

Jester preens and says her goodbyes, planning her strategy. 

~*~

It’s not difficult to crawl into bed beside Caleb when they’re both off window duty. Reaching down and grasping his cock does provoke a frantic whispered conversation though. 

“Jester, we shouldn’t –” Caleb glances over at Essek by the window. 

“Caleb I’m so _bored_ ,” Jester whines. “And I miss you. I miss this.” She strokes meaningfully between his legs. “Please?”

Caleb groans. “I can’t deny you anything, you know that.” He shifts. “We should try to be quiet though, if we can.”

Jester has never been one for silence in bed. She rides Caleb mercilessly, wringing several sounds from him. She can’t help but moan in response to his touches. 

Glancing over, she notices Essek’s ears have gone red, though he’s steadfastly looking out the window. 

Caleb comes first, and promptly busies himself between Jester’s legs, making sure she’s not far behind. 

Jester curls up against him and sleeps, a smile on her lips. She noticed Essek shifting in the chair by the window several times. 

~*~

When they’re next off duty together and Caleb is at the window, Jester offers to play chess with Essek.

Essek frowns, as if seeking some hidden insult, but agrees. 

Jester plays black, and Essek white.

“The Sicilian Defense,” Essek raises his eyebrows. “Interesting.”

“Did you think this was going to be easy?” Jester grins. “I had to go undercover once at a chess match, and pass as a player. I ended up in one of the final matches.”

They’re quiet for much of the game, musing over the board and pieces. Essek is cautious, while Jester is somewhat chaotic, making unexpected and nontraditional moves, startling him out of his predictions. 

“You are either reckless, or brilliant,” Essek says as she claims one of his bishops. 

“I could be both!” Jester shrugs. 

“You could be.” Essek advances a rook. “Check.”

Jester evades the checkmate peril. Eventually they come to a standstill. 

“Draw?” Essek offers. 

“Sure!” Jester shakes his hand. “Again?”

This time Jester plays white, Essek black. 

“So, have you had any lovers?” Jester asks, circling one of his rooks. 

Essek coughs. “Excuse me?”

“Lovers. You’ve been a spy for a long time, longer than me. Caleb’s had lovers. Has he told you about them?”

“… yes.” Essek looks down sharply at the board. 

“That’s good! I’ve met some of them. Astrid was my favorite, she was so pretty! The way she cut her hair, the way she lined up a shot … so cool. And she made Caleb happy.” Jester toys with one of the captured pawns. “When someone makes Caleb happy, that makes me happy too. Do you understand?” 

Essek looks up at her. “I … I think so.”

“Good.” Jester moves one of her knights forward. “Check.”

~*~

Despite reports to the contrary, Jester can in fact be patient. It takes rather a significant goal to aim for, but she can bide her time when necessary. 

Essek remains unswayed by the time their stakeout is concluded. Caleb looks disappointed, but Jester is determined. She’s noticed cracks in Essek’s façade, lingering glances when she or Caleb emerged from the shower, or were cuddling in bed. 

Fortunately the three of them are brought in for the interrogation of their quarry. Essek takes the lead while Caleb scribbles notes in the observation room and Jester relays information and tips to Essek via an earpiece. 

The interrogation is successful, and Essek returns to Jester and Caleb flush with triumph. 

“Feels strange, being on this side of things,” Essek looks through the mirror window. 

Jester shivers, remembering when Essek was hauled in last year. Turning him had been a joint effort between her and Caleb, with the looming threat of prison or death for Essek if he refused to cooperate giving them all strong motivation. 

“Do you regret your choice?” Caleb asks, in a way Jester finds refreshingly blunt. 

“At first, a little.” Essek admits. “Not any more though. The work I do now is much more satisfying. And the two of you …” he cuts himself off. 

“Yes?” Jester pipes up. “The two of us … what?”

“I cannot deny I have developed feelings for both of you.” Essek looks at them. “You are both accomplished agents. If this is some trick, some ploy, to ensure my loyalty, I assure you that is not necessary.”

“Essek, no!” Jester recoils at the idea. “Gross, I would never!” 

“While our superiors often ask much of us, that is not a service we provide.” Caleb’s voice is firm. “Which is part of why I am here, and not elsewhere.” 

“Oh.” Essek looks relieved and surprised all at once. “I … I don’t know what to say.”

“Well, you could say ‘Jester, kiss me now so I stop saying awful things’ for a start?” Jester suggests. “Or Caleb. Or both of us.”

Caleb steps forward, hesitating before Essek nods in assent. Then he kisses Essek. 

Jester has seen Caleb kiss other people before. She always wants to draw the sight, the way his head tilts and his hands grasp. 

When Caleb leans back, Essek’s eyes are wide and his lips still parted. 

“My turn,” Jester nudges Caleb to the side and stands on tiptoe to kiss Essek herself. He tastes like Caleb, and makes a soft moaning sound as she presses against him. Jester wants to make him louder, but she leans back as Caleb did, waiting for Essek to make the next move. 

“I think,” Essek is blushing again. “I think I would like to go somewhere with both of you. Somewhere with a bed. Somewhere that is not a hotel.”

“That,” Caleb says, holding up the keys to his town house “Can be arranged.”

“I’m driving!” Jester dashes for the door before either of them can protest. 

They don’t make it out of the car before the first round, but the night is still young.


End file.
